Construction of reverse vesicles from pseudo-graft poly(glycerol methacrylate)s via cyclodextrin–cholesterol interactions

Wen-Xing Gu; Ying-Wei Yang; Jijie Wen; Hongguang Lu; Hui Gao

doi:10.1039/c4py00848k

Construction of reverse vesicles based on cyclodextrin–cholesterol inclusion complexation

Journal of Controlled Release ◽

10.1016/j.jconrel.2015.05.193 ◽

2015 ◽

Vol 213 ◽

pp. e115

Author(s):

Wen-Xing Gu ◽

Ying-Wei Yang ◽

Ji-Jie Wen ◽

Hui Gao

Keyword(s):

Inclusion Complexation ◽

Reverse Vesicles

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Bottom-up Evolution from Disks to High-Genus Polymersomes

10.26434/chemrxiv.6108467.v1 ◽

2018 ◽

Author(s):

Claudia Contini ◽

Russell Pearson ◽

Linge Wang ◽

Lea Messager ◽

Jens Gaitzsch ◽

...

Keyword(s):

Self Assembly ◽

The Self ◽

Amphiphilic Copolymers ◽

Chain Entanglement ◽

Bottom Up ◽

New Approach ◽

High Genus ◽

Transmission Electron ◽

Minimal Radius ◽

Stop Flow

<div><div><div><p>We report the design of polymersomes using a bottom-up approach where the self-assembly of amphiphilic copolymers poly(2-(methacryloyloxy) ethyl phosphorylcholine)–poly(2-(diisopropylamino) ethyl methacrylate) (PMPC-PDPA) into membranes is tuned using pH and temperature. We study this process in detail using transmission electron microscopy (TEM), nuclear magnetic resonance (NMR) spectroscopy, dynamic light scattering (DLS), and stop-flow ab- sorbance disclosing the molecular and supramolecular anatomy of each structure observed. We report a clear evolution from disk micelles to vesicle to high-genus vesicles where each passage is controlled by pH switch or temperature. We show that the process can be rationalised adapting membrane physics theories disclosing important scaling principles that allow the estimation of the vesiculation minimal radius as well as chain entanglement and coupling. This allows us to propose a new approach to generate nanoscale vesicles with genus from 0 to 70 which have been very elusive and difficult to control so far.</p></div></div></div>

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Bottom-up Evolution from Disks to High-Genus Polymersomes

10.26434/chemrxiv.6108467 ◽

2018 ◽

Author(s):

Claudia Contini ◽

Russell Pearson ◽

Linge Wang ◽

Lea Messager ◽

Jens Gaitzsch ◽

...

Keyword(s):

Self Assembly ◽

The Self ◽

Amphiphilic Copolymers ◽

Chain Entanglement ◽

Bottom Up ◽

New Approach ◽

High Genus ◽

Transmission Electron ◽

Minimal Radius ◽

Stop Flow

<div><div><div><p>We report the design of polymersomes using a bottom-up approach where the self-assembly of amphiphilic copolymers poly(2-(methacryloyloxy) ethyl phosphorylcholine)–poly(2-(diisopropylamino) ethyl methacrylate) (PMPC-PDPA) into membranes is tuned using pH and temperature. We study this process in detail using transmission electron microscopy (TEM), nuclear magnetic resonance (NMR) spectroscopy, dynamic light scattering (DLS), and stop-flow ab- sorbance disclosing the molecular and supramolecular anatomy of each structure observed. We report a clear evolution from disk micelles to vesicle to high-genus vesicles where each passage is controlled by pH switch or temperature. We show that the process can be rationalised adapting membrane physics theories disclosing important scaling principles that allow the estimation of the vesiculation minimal radius as well as chain entanglement and coupling. This allows us to propose a new approach to generate nanoscale vesicles with genus from 0 to 70 which have been very elusive and difficult to control so far.</p></div></div></div>

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Synthesis of Amphiphilic Copolymers of Acrylic Acid and Styrene with the Desired Microstructure and Their Properties

Polymer Science Series B ◽

10.1134/s1560090420060081 ◽

2020 ◽

Vol 62 (6) ◽

pp. 649-659

Author(s):

K. O. Mineeva ◽

N. I. Osipova ◽

S. D. Zaitsev ◽

A. V. Plutalova ◽

E. I. Medentseva ◽

...

Keyword(s):

Acrylic Acid ◽

Amphiphilic Copolymers

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Cyclodextrin-Based Supramolecular Complexes of Osteoinductive Agents for Dental Tissue Regeneration

Pharmaceutics ◽

10.3390/pharmaceutics13020136 ◽

2021 ◽

Vol 13 (2) ◽

pp. 136

Author(s):

Masahiko Terauchi ◽

Atsushi Tamura ◽

Yoshinori Arisaka ◽

Hiroki Masuda ◽

Tetsuya Yoda ◽

...

Keyword(s):

Growth Factors ◽

Bone Formation ◽

Small Molecule ◽

Tissue Regeneration ◽

Alveolar Bone ◽

Inclusion Complexation ◽

Dental Tissue ◽

Polyelectrolyte Complexes ◽

Small Molecule Drugs

Oral tissue regeneration has received growing attention for improving the quality of life of patients. Regeneration of oral tissues such as alveolar bone and widely defected bone has been extensively investigated, including regenerative treatment of oral tissues using therapeutic cells and growth factors. Additionally, small-molecule drugs that promote bone formation have been identified and tested as new regenerative treatment. However, treatments need to progress to realize successful regeneration of oral functions. In this review, we describe recent progress in development of regenerative treatment of oral tissues. In particular, we focus on cyclodextrin (CD)-based pharmaceutics and polyelectrolyte complexation of growth factors to enhance their solubility, stability, and bioactivity. CDs can encapsulate hydrophobic small-molecule drugs into their cavities, resulting in inclusion complexes. The inclusion complexation of osteoinductive small-molecule drugs improves solubility of the drugs in aqueous solutions and increases in vitro osteogenic differentiation efficiency. Additionally, various anionic polymers such as heparin and its mimetic polymers have been developed to improve stability and bioactivity of growth factors. These polymers protect growth factors from deactivation and degradation by complex formation through electrostatic interaction, leading to potentiation of bone formation ability. These approaches using an inclusion complex and polyelectrolyte complexes have great potential in the regeneration of oral tissues.

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ß-Cyclodextrin Inclusion Complexes with Catechol-Containing Antioxidants Protocatechuic Aldehyde and Protocatechuic Acid—An Atomistic Perspective on Structural and Thermodynamic Stabilities

Molecules ◽

10.3390/molecules26123574 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3574

Author(s):

Thammarat Aree

Keyword(s):

Inclusion Complexes ◽

Protocatechuic Acid ◽

Inclusion Complexation ◽

Geometry Optimization ◽

Therapeutic Effects ◽

Full Geometry Optimization ◽

Oh Groups ◽

X Ray ◽

Protocatechuic Aldehyde ◽

Crystal Contacts

Protocatechuic aldehyde (PCAL) and protocatechuic acid (PCAC) are catechol derivatives and have broad therapeutic effects associated with their antiradical activity. Their pharmacological and physicochemical properties have been improved via the cyclodextrin (CD) encapsulation. Because the characteristics of b-CD inclusion complexes with PCAL (1) and PCAC (2) are still equivocal, we get to the bottom of the inclusion complexation by an integrated study of single-crystal X-ray diffraction and DFT full-geometry optimization. X-ray analysis unveiled that PCAL and PCAC are nearly totally shielded in the b-CD wall. Their aromatic rings are vertically aligned in the b-CD cavity such that the functional groups on the opposite side of the ring (3,4-di(OH) and 1-CHO/1-COOH groups) are placed nearby the O6–H and O2–H/O3–H rims, respectively. The preferred inclusion modes in 1 and 2 help to establish crystal contacts of OH×××O H-bonds with the adjacent b-CD OH groups and water molecules. By contrast, the DFT-optimized structures of both complexes in the gas phase are thermodynamically stable via the four newly formed host–guest OH⋯O H-bonds. The intermolecular OH×××O H-bonds between PCAL/PCAC 3,4-di(OH) and b-CD O6–H groups, and the shielding of OH groups in the b-CD wall help to stabilize these antioxidants in the b-CD cavity, as observed in our earlier studies. Moreover, PCAL and PCAC in distinct lattice environments are compared for insights into their structural flexibility.

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NMR studies of inclusion complexation of the pyrrolizidine alkaloid retronecine and p-sulfonic acid calix[6]arene

Journal of Inclusion Phenomena and Macrocyclic Chemistry ◽

10.1007/s10847-010-9825-1 ◽

2010 ◽

Vol 69 (1-2) ◽

pp. 149-155 ◽

Cited By ~ 17

Author(s):

Daniel Leite Silva ◽

Eder Couto Tavares ◽

Leila Souza Conegero ◽

Ângelo Fátima ◽

Ronaldo Aloise Pilli ◽

...

Keyword(s):

Sulfonic Acid ◽

Pyrrolizidine Alkaloid ◽

Inclusion Complexation ◽

Nmr Studies

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Bodipy-Loaded Micelles Based on Polylactide as Surface Coating for Photodynamic Control of Staphylococcus aureus

Coatings ◽

10.3390/coatings11020223 ◽

2021 ◽

Vol 11 (2) ◽

pp. 223

Author(s):

Enrico Caruso ◽

Viviana Teresa Orlandi ◽

Miryam Chiara Malacarne ◽

Eleonora Martegani ◽

Chiara Scanferla ◽

...

Keyword(s):

Staphylococcus Aureus ◽

Pathogenic Bacteria ◽

Surface Coatings ◽

Supramolecular System ◽

Amphiphilic Copolymers ◽

Oxygen Penetration ◽

Short Period ◽

Excellent Activity ◽

Coating Matrix ◽

Photodynamic Control

Decontaminating coating systems (DCSs) represent a challenge against pathogenic bacteria that may colonize hospital surfaces, causing several important infections. In this respect, surface coatings comprising photosensitizers (PSs) are promising but still controversial for several limitations. PSs act through a mechanism of antimicrobial photodynamic inactivation (aPDI) due to formation of reactive oxygen species (ROS) after light irradiation. However, ROS are partially deactivated during their diffusion through a coating matrix; moreover, coatings should allow oxygen penetration that in contact with the activated PS would generate 1O2, an active specie against bacteria. In the attempt to circumvent such constraints, we report a spray DCS made of micelles loaded with a PS belonging to the BODIPY family (2,6-diiodo-1,3,5,7-tetramethyl-8-(2,6-dichlorophenyl)-4,4′-difluoroboradiazaindacene) that is released in a controlled manner and then activated outside the coating. For this aim, we synthesized several amphiphilic copolymers (mPEG–(PLA)n), which form micelles, and established the most stable supramolecular system in terms of critical micelle concentration (CMC) and ∆Gf values. We found that micelles obtained from mPEG–(PLLA)2 were the most thermodynamically stable and able to release BODIPY in a relatively short period of time (about 80% in 6 h). Interestingly, the BODIPY released showed excellent activity against Staphylococcus aureus even at micromolar concentrations.

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Poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) Amphiphilic Copolymers for Long-Acting Injectables: Synthesis, Non-Acylating Performance and In Vivo Degradation

Molecules ◽

10.3390/molecules26051438 ◽

2021 ◽

Vol 26 (5) ◽

pp. 1438

Author(s):

Silvio Curia ◽

Feifei Ng ◽

Marie-Emérentienne Cagnon ◽

Victor Nicoulin ◽

Adolfo Lopez-Noriega

Keyword(s):

Ethylene Glycol ◽

Ring Opening ◽

Gel Chromatography ◽

Amphiphilic Copolymers ◽

Trimethylene Carbonate ◽

Poly Ethylene Glycol ◽

Poly Ethylene ◽

Long Acting ◽

In Vivo Degradation

This article presents the evaluation of diblock and triblock poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) amphiphilic copolymers (PEG-PTMCs) as excipients for the formulation of long-acting injectables (LAIs). Copolymers were successfully synthesised through bulk ring-opening polymerisation. The concomitant formation of PTMC homopolymer could not be avoided irrespective of the catalyst amount, but the by-product could easily be removed by gel chromatography. Pure PEG-PTMCs undergo faster erosion in vivo than their corresponding homopolymer. Furthermore, these copolymers show outstanding stability compared to their polyester analogues when formulated with amine-containing reactive drugs, which makes them particularly suitable as LAIs for the sustained release of drugs susceptible to acylation.

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